NPASS Compound

Structure

CID293629 OpenBabel06191716102D 44 48 0 0 1 0 0 0 0 0999 V2000 5.1962 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.5263 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.5263 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.0622 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.7942 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 2.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4641 3.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5981 2.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5981 -4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 38 1 0 0 0 0 3 39 1 0 0 0 0 4 5 2 0 0 0 0 4 12 1 0 0 0 0 5 16 1 0 0 0 0 6 12 2 0 0 0 0 6 18 1 0 0 0 0 7 13 2 0 0 0 0 7 14 1 0 0 0 0 8 13 1 0 0 0 0 8 19 2 0 0 0 0 9 15 1 0 0 0 0 9 17 1 0 0 0 0 10 40 1 0 0 0 0 11 1 1 6 0 0 0 11 22 1 0 0 0 0 11 41 1 0 0 0 0 13 42 1 0 0 0 0 14 21 2 0 0 0 0 14 30 1 0 0 0 0 15 21 1 0 0 0 0 15 31 2 0 0 0 0 16 18 2 0 0 0 0 16 38 1 0 0 0 0 17 12 1 1 0 0 0 17 43 1 0 0 0 0 18 39 1 0 0 0 0 19 21 1 0 0 0 0 19 43 1 0 0 0 0 20 10 1 1 0 0 0 20 23 1 0 0 0 0 20 44 1 0 0 0 0 22 24 1 0 0 0 0 22 32 1 1 0 0 0 23 25 1 0 0 0 0 23 33 1 6 0 0 0 24 26 1 0 0 0 0 24 34 1 6 0 0 0 25 27 1 0 0 0 0 25 35 1 1 0 0 0 26 28 1 0 0 0 0 26 36 1 6 0 0 0 27 29 1 0 0 0 0 27 37 1 6 0 0 0 28 40 1 1 0 0 0 28 41 1 0 0 0 0 29 42 1 1 0 0 0 29 44 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	624.21
Volume:	580.756
LogP:	1.02
LogD:	0.32
LogS:	-3.691
# Rotatable Bonds:	8
TPSA:	223.29
# H-Bond Aceptor:	15
# H-Bond Donor:	7
# Rings:	5
# Heavy Atoms:	15

MedChem Properties

QED Drug-Likeness Score:	0.19
Synthetic Accessibility Score:	4.755
Fsp3:	0.552
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.569
MDCK Permeability:	6.195115565788001e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.999
Human Intestinal Absorption (HIA):	0.769
20% Bioavailability (F20%):	0.001
30% Bioavailability (F30%):	0.985

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.125
Plasma Protein Binding (PPB):	61.166114807128906%
Volume Distribution (VD):	0.554
Pgp-substrate:	19.518964767456055%

ADMET: Metabolism

CYP1A2-inhibitor:	0.016
CYP1A2-substrate:	0.302
CYP2C19-inhibitor:	0.035
CYP2C19-substrate:	0.626
CYP2C9-inhibitor:	0.011
CYP2C9-substrate:	0.255
CYP2D6-inhibitor:	0.05
CYP2D6-substrate:	0.213
CYP3A4-inhibitor:	0.028
CYP3A4-substrate:	0.066

ADMET: Excretion

Clearance (CL):	1.704
Half-life (T1/2):	0.333

ADMET: Toxicity

hERG Blockers:	0.151
Human Hepatotoxicity (H-HT):	0.233
Drug-inuced Liver Injury (DILI):	0.953
AMES Toxicity:	0.46
Rat Oral Acute Toxicity:	0.102
Maximum Recommended Daily Dose:	0.017
Skin Sensitization:	0.682
Carcinogencity:	0.632
Eye Corrosion:	0.003
Eye Irritation:	0.037
Respiratory Toxicity:	0.879

Download Data

Data Type	Select
General Info & Identifiers & Properties
Structure MOL file
Source Organisms
Biological Activities
Similar NPs/Drugs

Natural Product: NPC293629

Natural Product ID:	NPC293629
*Common Name:**	(2S)-2-(3,4-Dimethoxyphenyl)-5-Hydroxy-7-[(2S,3R,4S,5S,6R)-3,4,5-Trihydroxy-6-[[(2R,3R,4R,5R,6S)-3,4,5-Trihydroxy-6-Methyloxan-2-Yl]Oxymethyl]Oxan-2-Yl]Oxy-2,3-Dihydrochromen-4-One
IUPAC Name:	(2S)-2-(3,4-dimethoxyphenyl)-5-hydroxy-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-2-yl]oxy-2,3-dihydrochromen-4-one
Synonyms:
Standard InCHIKey:	GUMSHIGGVOJLBP-SLRPQMTOSA-N
Standard InCHI:	InChI=1S/C29H36O15/c1-11-22(32)24(34)26(36)28(41-11)40-10-20-23(33)25(35)27(37)29(44-20)42-13-7-14(30)21-15(31)9-17(43-19(21)8-13)12-4-5-16(38-2)18(6-12)39-3/h4-8,11,17,20,22-30,32-37H,9-10H2,1-3H3/t11-,17-,20+,22-,23+,24+,25-,26+,27+,28+,29+/m0/s1
SMILES:	C[C@H]1[C@@H]([C@H]([C@H]([C@H](OC[C@@H]2[C@H]([C@@H]([C@H]([C@H](Oc3cc(c4C(=O)C[C@@H](c5ccc(c(c5)OC)OC)Oc4c3)O)O2)O)O)O)O1)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3184988
PubChem CID:	5284419
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid O-glycosides [CHEMONTID:0003533] Flavonoid-7-O-glycosides

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO3477	Plantago asiatica	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[2488968]
NPO3477	Plantago asiatica	Species	Plantaginaceae	Eukaryota	n.a.	seed	n.a.	PMID[2610694]
NPO8918	Plantago depressa	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26562611]
NPO8918	Plantago depressa	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3477	Plantago asiatica	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8918	Plantago depressa	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3477	Plantago asiatica	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8918	Plantago depressa	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO3477	Plantago asiatica	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO3477	Plantago asiatica	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO8918	Plantago depressa	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO8918	Plantago depressa	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3477	Plantago asiatica	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
Potency	8

Activity Type	# Activity
Others	8

Target ID	Target Type	Target Name	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified	Potency	n.a.	21786.8	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	Potency	n.a.	66212.6	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	Potency	n.a.	59012.1	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	Potency	n.a.	5949.5	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	Potency	n.a.	68310.7	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	Potency	n.a.	53024.9	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	Potency	n.a.	46875	nM	PubChem BioAssay data set

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available in NPASS)

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

● The left chart: Distribution of similarity level between NPC293629 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	410
0.1-0.2	1586
0.2-0.3	3515
0.3-0.4	8500
0.4-0.5	9174
0.5-0.6	4980
0.6-0.7	5034
0.7-0.8	6084
0.8-0.85	2161
0.85-0.9	894
0.9-0.95	344
0.95-1	15

Similarity Score	Similarity Level	Natural Product ID
0.9937	High Similarity	NPC105095
0.9937	High Similarity	NPC44328
0.9937	High Similarity	NPC177731
0.9937	High Similarity	NPC79056
0.9874	High Similarity	NPC43587
0.9753	High Similarity	NPC102028
0.9752	High Similarity	NPC267254
0.975	High Similarity	NPC61791
0.975	High Similarity	NPC195257
0.975	High Similarity	NPC105283
0.975	High Similarity	NPC209296
0.9748	High Similarity	NPC236934
0.9748	High Similarity	NPC5778
0.9691	High Similarity	NPC208668
0.9691	High Similarity	NPC239549
0.9691	High Similarity	NPC236191
0.9691	High Similarity	NPC51774
0.9689	High Similarity	NPC51326
0.9689	High Similarity	NPC293004
0.9689	High Similarity	NPC231194
0.9686	High Similarity	NPC284277
0.9686	High Similarity	NPC475366
0.9686	High Similarity	NPC475497
0.9632	High Similarity	NPC198199
0.9632	High Similarity	NPC142996
0.963	High Similarity	NPC180918
0.963	High Similarity	NPC301683
0.963	High Similarity	NPC156977
0.963	High Similarity	NPC256760
0.963	High Similarity	NPC261254
0.9627	High Similarity	NPC229687
0.9627	High Similarity	NPC472383
0.9627	High Similarity	NPC86008
0.9627	High Similarity	NPC472381
0.9625	High Similarity	NPC210073
0.9625	High Similarity	NPC70441
0.9625	High Similarity	NPC115674
0.9623	High Similarity	NPC29830
0.9623	High Similarity	NPC309025
0.9623	High Similarity	NPC243930
0.9623	High Similarity	NPC88023
0.9573	High Similarity	NPC48984
0.9573	High Similarity	NPC255799
0.9571	High Similarity	NPC204693
0.9568	High Similarity	NPC52353
0.9568	High Similarity	NPC21190
0.9568	High Similarity	NPC44558
0.9568	High Similarity	NPC150767
0.9568	High Similarity	NPC183357
0.9568	High Similarity	NPC194483
0.9568	High Similarity	NPC78734
0.9568	High Similarity	NPC22195
0.9565	High Similarity	NPC477502
0.9565	High Similarity	NPC229729
0.9565	High Similarity	NPC93099
0.9565	High Similarity	NPC45400
0.9563	High Similarity	NPC15358
0.9563	High Similarity	NPC311830
0.9563	High Similarity	NPC22832
0.956	High Similarity	NPC300537
0.956	High Similarity	NPC127782
0.9557	High Similarity	NPC271270
0.9557	High Similarity	NPC142860
0.9557	High Similarity	NPC97285
0.9557	High Similarity	NPC246469
0.9515	High Similarity	NPC251417
0.9515	High Similarity	NPC120952
0.9515	High Similarity	NPC89052
0.9512	High Similarity	NPC19108
0.9512	High Similarity	NPC220173
0.9512	High Similarity	NPC473327
0.9512	High Similarity	NPC16194
0.9512	High Similarity	NPC294815
0.9512	High Similarity	NPC476472
0.9509	High Similarity	NPC475155
0.9509	High Similarity	NPC472386
0.9506	High Similarity	NPC95855
0.9506	High Similarity	NPC170675
0.9506	High Similarity	NPC52382
0.9506	High Similarity	NPC270578
0.9506	High Similarity	NPC471457
0.9506	High Similarity	NPC210042
0.9506	High Similarity	NPC112755
0.9503	High Similarity	NPC8856
0.95	High Similarity	NPC19709
0.95	High Similarity	NPC191306
0.95	High Similarity	NPC270335
0.95	High Similarity	NPC284960
0.95	High Similarity	NPC222936
0.9497	High Similarity	NPC182045
0.9458	High Similarity	NPC192539
0.9455	High Similarity	NPC292019
0.9455	High Similarity	NPC202908
0.9455	High Similarity	NPC219043
0.9455	High Similarity	NPC122467
0.9455	High Similarity	NPC14187
0.9451	High Similarity	NPC25724
0.9448	High Similarity	NPC210808
0.9448	High Similarity	NPC67105
0.9448	High Similarity	NPC218488
0.9448	High Similarity	NPC105511
0.9448	High Similarity	NPC34287
0.9448	High Similarity	NPC471416
0.9448	High Similarity	NPC199079
0.9448	High Similarity	NPC474434
0.9448	High Similarity	NPC95866
0.9448	High Similarity	NPC285197
0.9444	High Similarity	NPC160156
0.9444	High Similarity	NPC92565
0.9441	High Similarity	NPC165720
0.9437	High Similarity	NPC189142
0.9437	High Similarity	NPC77660
0.9437	High Similarity	NPC190450
0.9437	High Similarity	NPC473043
0.9437	High Similarity	NPC148273
0.9434	High Similarity	NPC110349
0.9398	High Similarity	NPC472387
0.9398	High Similarity	NPC173837
0.9398	High Similarity	NPC475261
0.9398	High Similarity	NPC241196
0.9394	High Similarity	NPC294629
0.939	High Similarity	NPC155877
0.939	High Similarity	NPC134532
0.939	High Similarity	NPC471748
0.939	High Similarity	NPC203259
0.939	High Similarity	NPC48773
0.939	High Similarity	NPC259152
0.939	High Similarity	NPC47140
0.939	High Similarity	NPC288152
0.939	High Similarity	NPC137871
0.939	High Similarity	NPC257011
0.939	High Similarity	NPC33054
0.939	High Similarity	NPC235575
0.939	High Similarity	NPC3583
0.939	High Similarity	NPC9002
0.939	High Similarity	NPC471725
0.939	High Similarity	NPC307518
0.939	High Similarity	NPC60735
0.939	High Similarity	NPC26230
0.939	High Similarity	NPC67134
0.939	High Similarity	NPC176740
0.939	High Similarity	NPC205076
0.9387	High Similarity	NPC201292
0.9387	High Similarity	NPC226294
0.9387	High Similarity	NPC469931
0.9387	High Similarity	NPC186807
0.9387	High Similarity	NPC45638
0.9387	High Similarity	NPC93337
0.9387	High Similarity	NPC203050
0.9387	High Similarity	NPC105025
0.9387	High Similarity	NPC219904
0.9387	High Similarity	NPC183036
0.9387	High Similarity	NPC227508
0.9387	High Similarity	NPC225434
0.9387	High Similarity	NPC58053
0.9387	High Similarity	NPC223747
0.9387	High Similarity	NPC120099
0.9387	High Similarity	NPC475942
0.9383	High Similarity	NPC21100
0.9383	High Similarity	NPC197285
0.9379	High Similarity	NPC88043
0.9379	High Similarity	NPC124155
0.9379	High Similarity	NPC168822
0.9379	High Similarity	NPC257566
0.9375	High Similarity	NPC303913
0.9371	High Similarity	NPC22062
0.9371	High Similarity	NPC138811
0.9371	High Similarity	NPC473634
0.9367	High Similarity	NPC206378
0.9341	High Similarity	NPC473682
0.9341	High Similarity	NPC470443
0.9341	High Similarity	NPC473895
0.9341	High Similarity	NPC241423
0.9341	High Similarity	NPC470444
0.9341	High Similarity	NPC110941
0.9341	High Similarity	NPC473571
0.9341	High Similarity	NPC126784
0.9337	High Similarity	NPC169733
0.9337	High Similarity	NPC471669
0.9337	High Similarity	NPC89127
0.9337	High Similarity	NPC472384
0.9337	High Similarity	NPC472380
0.9337	High Similarity	NPC472382
0.9333	High Similarity	NPC472993
0.9329	High Similarity	NPC67326
0.9329	High Similarity	NPC136042
0.9329	High Similarity	NPC212748
0.9329	High Similarity	NPC156869
0.9329	High Similarity	NPC206123
0.9329	High Similarity	NPC224462
0.9329	High Similarity	NPC29958
0.9329	High Similarity	NPC259896
0.9329	High Similarity	NPC255157
0.9329	High Similarity	NPC254855
0.9325	High Similarity	NPC116745
0.9325	High Similarity	NPC275454
0.9325	High Similarity	NPC226304
0.9325	High Similarity	NPC84362
0.9325	High Similarity	NPC146792
0.9325	High Similarity	NPC325555

Chemically structural similarity: II. Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC293629 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	363
0.1-0.2	906
0.2-0.3	1824
0.3-0.4	2628
0.4-0.5	1887
0.5-0.6	972
0.6-0.7	398
0.7-0.8	126
0.8-0.85	30
0.85-0.9	10
0.9-0.95	5
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9937	High Similarity	NPD7074	Phase 3
0.975	High Similarity	NPD7054	Approved
0.9689	High Similarity	NPD7472	Approved
0.9512	High Similarity	NPD7808	Phase 3
0.9451	High Similarity	NPD7251	Discontinued
0.939	High Similarity	NPD6797	Phase 2
0.9207	High Similarity	NPD3818	Discontinued
0.9202	High Similarity	NPD6166	Phase 2
0.9202	High Similarity	NPD6168	Clinical (unspecified phase)
0.9202	High Similarity	NPD6167	Clinical (unspecified phase)
0.9187	High Similarity	NPD4381	Clinical (unspecified phase)
0.9152	High Similarity	NPD7804	Clinical (unspecified phase)
0.9057	High Similarity	NPD1934	Approved
0.9048	High Similarity	NPD4338	Clinical (unspecified phase)
0.8882	High Similarity	NPD2393	Clinical (unspecified phase)
0.865	High Similarity	NPD2801	Approved
0.8598	High Similarity	NPD3817	Phase 2
0.858	High Similarity	NPD4380	Phase 2
0.8547	High Similarity	NPD6559	Discontinued
0.8545	High Similarity	NPD4868	Clinical (unspecified phase)
0.8494	Intermediate Similarity	NPD7075	Discontinued
0.8438	Intermediate Similarity	NPD1511	Approved
0.8434	Intermediate Similarity	NPD3882	Suspended
0.8393	Intermediate Similarity	NPD5494	Approved
0.8382	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD1512	Approved
0.8313	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8291	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8291	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8263	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8239	Intermediate Similarity	NPD1549	Phase 2
0.8235	Intermediate Similarity	NPD6959	Discontinued
0.8208	Intermediate Similarity	NPD7228	Approved
0.8204	Intermediate Similarity	NPD7819	Suspended
0.8161	Intermediate Similarity	NPD5844	Phase 1
0.816	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.815	Intermediate Similarity	NPD7473	Discontinued
0.8144	Intermediate Similarity	NPD6801	Discontinued
0.8136	Intermediate Similarity	NPD8313	Approved
0.8136	Intermediate Similarity	NPD8312	Approved
0.8122	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8095	Intermediate Similarity	NPD1465	Phase 2
0.8084	Intermediate Similarity	NPD7411	Suspended
0.8081	Intermediate Similarity	NPD6232	Discontinued
0.8061	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.8047	Intermediate Similarity	NPD5402	Approved
0.8023	Intermediate Similarity	NPD7199	Phase 2
0.8012	Intermediate Similarity	NPD1653	Approved
0.8	Intermediate Similarity	NPD2796	Approved
0.7988	Intermediate Similarity	NPD6799	Approved
0.7952	Intermediate Similarity	NPD5403	Approved
0.7939	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7937	Intermediate Similarity	NPD1510	Phase 2
0.7921	Intermediate Similarity	NPD7685	Pre-registration
0.7912	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7898	Intermediate Similarity	NPD3751	Discontinued
0.7886	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7882	Intermediate Similarity	NPD8455	Phase 2
0.7874	Intermediate Similarity	NPD3787	Discontinued
0.7865	Intermediate Similarity	NPD8151	Discontinued
0.784	Intermediate Similarity	NPD7266	Discontinued
0.7831	Intermediate Similarity	NPD5401	Approved
0.7829	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7824	Intermediate Similarity	NPD37	Approved
0.7821	Intermediate Similarity	NPD7240	Approved
0.7811	Intermediate Similarity	NPD6599	Discontinued
0.7803	Intermediate Similarity	NPD6234	Discontinued
0.7799	Intermediate Similarity	NPD1240	Approved
0.7799	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7799	Intermediate Similarity	NPD1613	Approved
0.7791	Intermediate Similarity	NPD4966	Approved
0.7791	Intermediate Similarity	NPD4965	Approved
0.7791	Intermediate Similarity	NPD4967	Phase 2
0.7784	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD7783	Phase 2
0.7771	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.776	Intermediate Similarity	NPD7584	Approved
0.7747	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7725	Intermediate Similarity	NPD6781	Approved
0.7725	Intermediate Similarity	NPD6780	Approved
0.7725	Intermediate Similarity	NPD6779	Approved
0.7725	Intermediate Similarity	NPD6782	Approved
0.7725	Intermediate Similarity	NPD6776	Approved
0.7725	Intermediate Similarity	NPD6778	Approved
0.7725	Intermediate Similarity	NPD6777	Approved
0.7702	Intermediate Similarity	NPD1607	Approved
0.7696	Intermediate Similarity	NPD7698	Approved
0.7696	Intermediate Similarity	NPD7435	Discontinued
0.7696	Intermediate Similarity	NPD7696	Phase 3
0.7696	Intermediate Similarity	NPD7697	Approved
0.7688	Intermediate Similarity	NPD7768	Phase 2
0.764	Intermediate Similarity	NPD1933	Approved
0.7629	Intermediate Similarity	NPD7701	Phase 2
0.7627	Intermediate Similarity	NPD3926	Phase 2
0.761	Intermediate Similarity	NPD3027	Phase 3
0.76	Intermediate Similarity	NPD919	Approved
0.759	Intermediate Similarity	NPD3750	Approved
0.759	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.759	Intermediate Similarity	NPD4628	Phase 3
0.7578	Intermediate Similarity	NPD943	Approved
0.7576	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7565	Intermediate Similarity	NPD7870	Phase 2
0.7565	Intermediate Similarity	NPD7871	Phase 2
0.7562	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7552	Intermediate Similarity	NPD6823	Phase 2
0.7547	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7543	Intermediate Similarity	NPD3749	Approved
0.7526	Intermediate Similarity	NPD7699	Phase 2
0.7526	Intermediate Similarity	NPD7700	Phase 2
0.7514	Intermediate Similarity	NPD1247	Approved
0.7484	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7474	Intermediate Similarity	NPD8320	Phase 1
0.7474	Intermediate Similarity	NPD8319	Approved
0.7462	Intermediate Similarity	NPD7874	Approved
0.7462	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.746	Intermediate Similarity	NPD6534	Approved
0.746	Intermediate Similarity	NPD6535	Approved
0.7455	Intermediate Similarity	NPD2935	Discontinued
0.7455	Intermediate Similarity	NPD1551	Phase 2
0.7448	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD7458	Discontinued
0.7425	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7425	Intermediate Similarity	NPD6674	Discontinued
0.7424	Intermediate Similarity	NPD7801	Approved
0.7423	Intermediate Similarity	NPD447	Suspended
0.7423	Intermediate Similarity	NPD230	Phase 1
0.7412	Intermediate Similarity	NPD2532	Approved
0.7412	Intermediate Similarity	NPD2534	Approved
0.7412	Intermediate Similarity	NPD2533	Approved
0.7396	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7382	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.736	Intermediate Similarity	NPD7585	Approved
0.7349	Intermediate Similarity	NPD6099	Approved
0.7349	Intermediate Similarity	NPD6100	Approved
0.7337	Intermediate Similarity	NPD6190	Approved
0.7333	Intermediate Similarity	NPD7680	Approved
0.7326	Intermediate Similarity	NPD8150	Discontinued
0.7321	Intermediate Similarity	NPD2800	Approved
0.731	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD7583	Approved
0.7289	Intermediate Similarity	NPD3748	Approved
0.7283	Intermediate Similarity	NPD5953	Discontinued
0.7273	Intermediate Similarity	NPD6651	Approved
0.7268	Intermediate Similarity	NPD7286	Phase 2
0.7251	Intermediate Similarity	NPD7390	Discontinued
0.7241	Intermediate Similarity	NPD3226	Approved
0.7234	Intermediate Similarity	NPD8434	Phase 2
0.7225	Intermediate Similarity	NPD6212	Phase 3
0.7225	Intermediate Similarity	NPD920	Approved
0.7225	Intermediate Similarity	NPD6213	Phase 3
0.7225	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD6832	Phase 2
0.7222	Intermediate Similarity	NPD4908	Phase 1
0.7215	Intermediate Similarity	NPD1091	Approved
0.7204	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD4360	Phase 2
0.7188	Intermediate Similarity	NPD4363	Phase 3
0.7186	Intermediate Similarity	NPD7033	Discontinued
0.7176	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD5353	Approved
0.7134	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7127	Intermediate Similarity	NPD8127	Discontinued
0.7119	Intermediate Similarity	NPD6844	Discontinued
0.7118	Intermediate Similarity	NPD1243	Approved
0.711	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD6842	Approved
0.7105	Intermediate Similarity	NPD6841	Approved
0.7105	Intermediate Similarity	NPD6843	Phase 3
0.7101	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD2346	Discontinued
0.7101	Intermediate Similarity	NPD2344	Approved
0.7099	Intermediate Similarity	NPD2798	Approved
0.7093	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD2799	Discontinued
0.7083	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD7930	Approved
0.7055	Intermediate Similarity	NPD9494	Approved
0.7049	Intermediate Similarity	NPD5242	Approved
0.7045	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD1203	Approved
0.7033	Intermediate Similarity	NPD5619	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD2313	Discontinued
0.703	Intermediate Similarity	NPD6798	Discontinued
0.7024	Intermediate Similarity	NPD7097	Phase 1
0.702	Intermediate Similarity	NPD5006	Approved
0.702	Intermediate Similarity	NPD5005	Approved
0.7019	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD1652	Phase 2
0.7011	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD5124	Phase 1
0.7006	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD6355	Discontinued
0.7	Intermediate Similarity	NPD1610	Phase 2
0.6995	Remote Similarity	NPD5710	Approved
0.6995	Remote Similarity	NPD5711	Approved
0.6982	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD6386	Approved

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data